Cybermarc - If those panniers meet all your needs and you enjoyed making them that is awesome!
Personally I have limited tools/skills for fabricating my own gear. I do make small mods to things and I sometimes combine existing parts in ways unintended by the manufacturer, but that is about it.
I have two sets of Ortlieb panniers that cost ~$150 each. They work really well for me and I would not have been able to make a set that worked as well on my own. Heck I see panniers all the time that are made by factories that don't seem to be half as nice.
You mentioned that there isn't much challenge in ordering parts online and having a LBS build up a touring bike. This is true to an extent, but the only challenge really common to everyone on this forum is sitting on a touring bike and turning the pedals. Some people do zero bike maintenance yet they still tour. Some people carry zero gear and eat gourmet food at 5 star hotels every night. And of course some people weld their own frames, build their own panniers, cook their own food and travel the globe on a minimal budget. So what? I don't think how you tour or what your level of mechanical/fabrication skill is matters to anyone but you in the end.
I think it is great you enjoy your homemade panniers. Personally if I needed new panniers I'd be on the phone to an Ortlieb dealer ASAP. Does one of us deserve a medal and the other a derisive chuckle?
The hobo chic comment really comes down to whether you use your homemade gear and have fun or whether you need to make a big deal about it and get outside approval for it. If it is the latter it is hobo chic.
For what it is worth I live in the inner city and I have watched homeless people tear through donation bags outside a Goodwill making a huge pile of clothing and definitely only taking those items that fit their personal style.
And to be fair I will point out that I definitely care about bike chic. I built up a set of wheels taking care to order all black parts - I think it looks cool. I am waiting longer than necessary for a replacement surly LHT frame because I want the red colour not the blue. I sometimes look at my Ortlieb panniers and wish the rears were black like the fronts. I am definitely guilty of bike chic - but I still sleep really well at night...
